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Cheap flights from Montrose to Chicago from $155

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Montrose to Chicago departing on 1/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Montrose to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:30 pm - 12:05 amMTJ-MDW
5h 35m1 stop
Southwest Logo
8:00 am - 3:10 pmMDW-MTJ
8h 10m1 stop
$414Southwest
Find Deal
Thu, Dec 18 - Mon, Dec 22
Southwest Logo
11:50 am - 10:25 pmMTJ-MDW
9h 35m2 stops
Southwest Logo
8:00 am - 3:10 pmMDW-MTJ
8h 10m1 stop
$430Southwest
Find Deal
Thu, Dec 18 - Mon, Dec 22
Southwest Logo
11:50 am - 10:25 pmMTJ-MDW
9h 35m2 stops
Southwest Logo
5:25 am - 11:30 amMDW-MTJ
7h 05m2 stops
$449Southwest
Find Deal
Thu, Dec 18 - Mon, Dec 22
Southwest Logo
11:50 am - 8:10 pmMTJ-MDW
7h 20m1 stop
Southwest Logo
9:35 pm - 11:35 amMDW-MTJ
15h 00m2 stops
$580Southwest
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Sun, Nov 23 - Fri, Nov 28
Southwest Logo
11:50 am - 10:25 pmMTJ-MDW
9h 35m2 stops
Southwest Logo
9:35 pm - 11:35 amMDW-MTJ
15h 00m2 stops
$612Southwest
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Sun, Nov 23 - Fri, Nov 28
Delta Logo
3:08 pm - 10:22 pmMTJ-MDW
6h 14m1 stop
Delta Logo
6:00 am - 2:12 pmMDW-MTJ
9h 12m1 stop
$723Delta
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Sat, Dec 20 - Thu, Dec 25

Southwest flights from Montrose to Chicago Midway Airport

Our best Southwest deals on Montrose to Chicago Midway Airport flight tickets
Southwest
Dec 18
MTJ5:30 pmMontrose County
5h 35m
1 stop
MDW12:05 amChicago Midway
Dec 22
MDW8:00 amChicago Midway
8h 10m
1 stop
MTJ3:10 pmMontrose County
$414
Find similar
Southwest
Dec 18
MTJ11:50 amMontrose County
9h 35m
2 stops
MDW10:25 pmChicago Midway
Dec 22
MDW8:00 amChicago Midway
8h 10m
1 stop
MTJ3:10 pmMontrose County
$430
Find similar
Southwest
Dec 18
MTJ11:50 amMontrose County
9h 35m
2 stops
MDW10:25 pmChicago Midway
Dec 22
MDW5:25 amChicago Midway
7h 05m
2 stops
MTJ11:30 amMontrose County
$449
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Montrose to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated November 4, 2025.
Use the filters below to find and compare flights from Montrose to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Thu 12/18

5:30 pm-12:05 am

1 stop5h 35m

Chicago Midway

Mon 12/22

8:00 am-3:10 pm

1 stop8h 10m

$414

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Thu 12/18

11:50 am-10:25 pm

2 stops9h 35m

Chicago Midway

Mon 12/22

8:00 am-3:10 pm

1 stop8h 10m

$430

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Thu 12/18

11:50 am-10:25 pm

2 stops9h 35m

Chicago Midway

Mon 12/22

5:25 am-11:30 am

2 stops7h 05m

$449

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Sun 11/23

11:50 am-8:10 pm

1 stop7h 20m

Chicago Midway

Fri 11/28

9:35 pm-11:35 am

2 stops15h 00m

$580

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Sun 11/23

11:50 am-10:25 pm

2 stops9h 35m

Chicago Midway

Fri 11/28

9:35 pm-11:35 am

2 stops15h 00m

$612

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Sat 12/20

3:08 pm-10:22 pm

1 stop6h 14m

Chicago Midway

Thu 12/25

6:00 am-2:12 pm

1 stop9h 12m

$723

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Sat 1/24

9:50 am-4:25 pm

1 stop5h 35m

$155

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Sat 1/24

9:50 am-8:25 pm

2 stops9h 35m

$160

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Mon 3/9

8:20 am-1:50 pm

1 stop4h 30m

$200

MontroseChicago

MTJ - MDW

MTJMDW

Montrose County

Mon 3/9

8:20 am-5:50 pm

2 stops8h 30m

$205

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Montrose to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Montrose County to Chicago Midway?

Southwest and Delta are the most popular carriers operating from Montrose County to Chicago Midway

When to book flights from Montrose to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Montrose to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Montrose to Chicago Midway Airport (MTJ to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Montrose to Chicago Midway Airport

Direct flights

None
There are no direct flights from Montrose to Chicago Midway Airport. There are no popular flight routes from Montrose to Chicago Midway Airport.
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  • How far is Montrose County to Chicago Midway by plane?

    Montrose County and Chicago Midway are 1084.3 mi apart from one another. Typically, this will take 5h 35m by plane in normal conditions.

  • When did momondo last update prices for flights from Montrose County Airport to Chicago Midway Airport?

    Prices for flights from Montrose County Airport to Chicago Midway Airport were last updated today.

  • How old do you have to be to fly from Montrose County Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Montrose County Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Montrose to Chicago?

Finding the right flight to Chicago from Montrose is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Montrose to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Montrose to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Montrose to Chicago?

Once all potential Montrose to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Montrose to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Montrose to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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